In growing urban areas, populations are increasingly exposed to the effects of climate change. Rainwater has been identified as a primary risk, although it is also an opportunity to pursue resilient and equitable cities while regenerating the urban ecosystem. Both urban design and landscape ecology have attempted to define effective responses to urban flooding and their synergy supports novel transdisciplinary approaches. The translation of adaptive management theories to the design process suggests working with rainwater rather than defending against it, combining science and practice. This paper retraces the evolution of design for flooding approaches and outlines the basis of an adaptive urban design for rainwater management.